Not sure if this will help, but, I had a similar issue with Photobucket and Image Shack a few years ago and I switched to TinyPic and MediaFire after noticing many members of the forums I was on were using them also and I haven't had a problem since. Are the files of the same format?

Microsoft Community Contributor

Different formats and some are very small but it just stops after a while and times out. I've used Photo Bucket for a long time with out issues, but I was also having problems uploading a small file to the Adobe forums.

This only started a couple of days ago, I have a 100 mbs connection and this kind of thing is't usually and issue. But for the last few days I can only get a file to upload once in a while, one will go through and then the next one will fail 3 times in a row.

Currently I'm having an issue with my internet cutting in & out and I keep switching my ethernet cables to a different port, I thought it was my ISP as we were having phone problems, but now it seems like my modem/router is going bad. Have you checked yours? Or, have your ISP run a check.